Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde

路易斯酸配位逆转反应类型选择性:1-萘甲醛和2-萘甲醛的邻位光环加成反应

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Abstract

The value of a specific substrate class for synthetic applications is greatly enhanced if different types of reactions can be performed selectively upon a judicious choice of reaction conditions. In the present study it was shown that the typical photochemical behaviour of naphthaldehydes is completely altered in the presence of Lewis acids. Without Lewis acids, reactions at the carbonyl group are exclusively observed while Lewis acids facilitate a visible light-mediated cycloaddition at the arene core providing access to products of aromatic C-H functionalization via cyclobutane intermediates.

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